Fairfield Avenue runs along a natural ridge of land that is 159 feet above the Connecticut River and was once promoted as the "highest elevation in Hartford." The road was considered to be the main thoroughfare to Wethersfield and attracted leisure drivers with its sweeping vistas eastward and westward. In 1874 the Hartford Courant reported, "[Fairfield Avenue] commands from almost every rod of its entire distance a view of the Connecticut valley on the east and the fine stretch of country lying on the westa most sightly and beautiful landscape in either direction. It will make altogether the longest direct drive with unobstructed outlooks, and the most attractive too, that we have in Hartford, and that is saying a good deal...." Today, the avenue transects three of Hartford's neighborhoods: Barry Square and South End to the east, and the South West neighborhood to the west. In 2011, the entire length of the street was listed on the National Register of Historic Places.

During and after the Civil War, Hartford’s wealth and capital increased dramatically, and a new elite class of industrialists and insurance executives developed in the city. These men sought out desirable land on the outskirts of the city where they could construct glamorous and expansive homes illustrative of their financial successes. Among those was George A. Fairfield, a former employee of Samuel Colt, president of the Weed Sewing Machine Company and the Hartford Machine Screw Company, and respected community leader. In 1864, he purchased a small farmhouse with 32 acres of land on what was then Ridge Road, and soon transformed into a palatial estate. By the turn of the 20th century, the street had been renamed in his honor.

The estates were interspersed with what was mostly farmland, the largest being that of James H. Smith, whose expanse of land included 500 feet of frontage on Fairfield Avenue and extending some 175 feet back from the street. His elegant Queen Anne residence still stands today.

Between 1890 and 1900, the city's population increased tremendously, and new electric trolley lines radiated in all directions from the city's centerincluding one that ran out New Britain Avenue with a spur down Fairfield Avenue to Cedar Hill Cemetery. Dependable transportation made it possible to develop suburbs for middle-income and working-class families. A fact not overlooked by real estate developers. Once accessible to Hartford's middle class, real estate development along the avenue occurred with earnest. Land tract auctions on became more and more common and very popular resulting in many of the old estates and remaining farms being broken into smaller building lots or subdivisions such as Trinity Heights, Grandview, Broadview and Fairfield Park. When George Fairfield died in 1908, he left no will and his estate was, too, subject to being piecemealed by speculators and developors. All that is left today is his Italiante style home, which is now split up into condominiums.

In the early 20th century, Frederick Law Olmsted first outlined plans for a ring of parks surrounding the central city. Tree-lined Fairfield Avenue was seen as a greenway corridor to connect Pope Park, the new Rocky Ridge Park and Goodwin Park. The portion of Rocky Ridge Park south of New Britain Avenue was renamed the Thomas J.Hyland Park, in honor of a man who had organized youth sporting events in the neighborhood up until his untimely death in 1954. The park features baseball diamonds, a spray park and playground for kids and a basketball court.

Engine Company 15 (renamed the Mayor Mike Peters Fire Station) of the Hartford Fire Department is located at the northern end of the avenue. Built in 1909, it is the oldest extant firehouse in the city and is listed in its own right on the National Register of Historic Places. Behind the main floor apparatus room was a horse stable with eight stalls and a shower bath for the horses used to pull the fire wagons. Evidence of these stalls are still visible today.

Up until the late 1860s, the road was known by a number of names, including at one time or another, Rock Hill Avenue, Ridge Road and Rocky Hill Ridge Road. Over the course of more than two centuries of use Colonial travelers, farmers’ wagons, cemetery mourners, trolleys, and automobiles have traversed its surface; and woodlots, farms, mansions, and middle-class homes have sprouted along its flanks. It has alwaysand remains todaybeen seen as a desirable area in which to live.